Diisopropylethylamine → HCID 69258837, compound

HRID 898923Notes

Reaction equation

HRID 898923 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][NH:7][CH2:8][CH3:9])=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.Cl[C:22](=[O:44])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][O:33][C:34]2[CH:43]=[CH:42][CH:41]=[CH:40][C:35]=2[C:36]([O:38][CH3:39])=[O:37])=[CH:27][CH:26]=1>C(#N)C>[CH2:8]([N:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:11][CH:10]=1)[C:22](=[O:44])[CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][O:33][C:34]2[CH:43]=[CH:42][CH:41]=[CH:40][C:35]=2[C:36]([O:38][CH3:39])=[O:37])=[CH:29][CH:30]=1)[CH3:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4716481N-(4-fluorobenzyl)ethanamineHCID 86600967Benzoic acid, 2-[2-[4-(2-chloro-2-oxoethoxy)phenyl]ethoxy]-, methyl ester

Product 1

HCID 69258837HCID 69258837, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(4-Fluorobenzyl)ethanamine (0.114 g, 0.745 mmol) was dissolved in dry acetonitrile under N2 and N-ethyl-N,N-diisopropylamine (0.371 g, 2.867 nmol) was added. The mixture was stirred for 30 min and methyl 2-{2-[4-(2-chloro-2-oxoethoxy)phenyl]-ethoxy}benzoate (0.200 g, 0.573 mmol) was added. The solution was stirred overnight at room temperature. The crude was purified by flash chromatography (started with isocratic heptane/EtOAc 50/50 and then the EtOAc concentration was increased to 100%, (silica gel 60 0.004-0.063 mm). The product containing fractions were pooled and the EtOAc was removed by evaporation to give 0.223 g of methyl 2-[2-(4-{2-[ethyl(4-fluorobenzyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoate (yield 83.5%).

Workup

  1. stirringThe solution was stirred overnight at room temperature
  2. customThe crude was purified by flash chromatography (
  3. concentrationthe EtOAc concentration
  4. temperaturewas increased to 100%, (silica gel 60 0.004-0.063 mm)
  5. additionThe product containing fractions
  6. customthe EtOAc was removed by evaporation

Sources & evidence

ORD record
ord-52c5a162d1ed4a5387a2f293f7c5f508
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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